In the intaglio (the design is incised into the stone) Henry VIII (ruled 1509-1547) is shown full face with a fur-trimmed coat and a flat hat on his head. The letters 'H' and 'R' are engraved on either side of him. The intaglio must predate 1576 when an impression of it appears on a seal attached to a deed dated 31 October in the 18th year of Elizabeth I's reign (1558-1603), that is, 1576. The seal is that of Dorothy, wife of John Abingdon of Hindlip, Worcestershire, who was cofferer to the Queen.

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In his Life and Death of Cardinal Wolsey George Cavendish, who was a member of the Cardinal's household, relates that at Christmas 1529 Henry sent Wolsey a ring. Cardinal Wolsey (1473-1530) had been the King's chief minister, but he had recently fallen from favour. According to Cavendish, the ring 'was engraved with the King's visage within a ruby, as lively counterfeit as possible to be devised. This ring he knoweth well; for he gave me the same.' The ruby ring showing Henry VIII is not known to have survived. While the portrait of Henry engraved on the V&A's ring uses a similar technique, it must be later than the ring Cavendish describes, because the King is shown in late middle age, as in the 1540s, towards the end of his reign. It is not of high quality.

Elizabeth I probably gave this ring, set with a chalcedony portrait of Henry VIII, to a member of the Abingdon family. An impression of the intaglio can be found on a document of 1576 as the seal of Dorothy Abingdon (formerly Broadbelt), who served as one of the Queen's gentlewomen of the bedchamber from 1558 to 1557 and was included in the Queen's coronation procession. She was also keeper of the Queen's parrot and monkey. Her husband John Abingdon worked in the Counting House and became the Queen’s cofferer a year before his death in 1581. The Queen was godmother to their son Thomas. Dorothy's role as one of Elizabeth's closest servants gave her privileged access to the Queen. In 1562, the state papers reveal that she used this access to promote the possible marriage of the Queen to the Swedish King Eric, writing to Nicholas Guildenstern, the Swedish Chancellor to suggest that if the King were to renew his suit, it would be well received. The letter was intercepted by William Cecil and Dorothy and her fellow bedwoman Katherine Ashley were interrogated and confined to their chambers.

The warm relations between the Abingdons and the Tudor court did not persist. John Abingdon’s sons Edward and Thomas retained their allegiance to the Catholic faith. They became involved in the Babington Plot of 1586, to replace Elizabeth with the Catholic Mary Queen of Scots. Edward was executed for his part in the conspiracy but Thomas was spared, possibly because of his youth and his relationship with the Queen. His home, Hindlip Hall, became a shelter for recusant priests. After the discovery of the Gunpowder Plot in 1605, the Hall was searched. A contemporary account describes the discovery of “two cunning and very artificial conveyances in the main brick wall, so ingeniously framed and with such art, as it cost much labour ere they could be found. […] Eleven secret corners and conveyances were found in the said house, all of them having books, Massing stuff and Popish trumpery in them.” Although the Jesuits arrested at Hindlip were put to death, Thomas Abingdon was spared and spent the rest of his life as an antiquary.